How to get over the fear of failure when starting a business

Taking the leap from a 9-5 corporate job to freelancing full-time might just have been the scariest thing I’ve ever done. And I would guess that I’m not the only one who’s felt as if this transition was absolutely terrifying. After all, making the decision to buck traditionalism and start your own thing is fraught with more questions than answers when you first start considering this type of major life change.

The general questions entrepreneur hopefuls ask usually revolve around things that were once handled by the company they worked for: taxes, health insurance, retirement and so on. But the questions that really keep people up at night—and prevent the from taking actually starting their own business—are about the big picture, namely:

Do I have what it takes to turn my idea into reality?

Will people buy what I’m offering?

Will I be able to make enough money to make ends meet?

And, ultimately . . . will I fail?

Here’s the good news: everyone who’s gone through the process of becoming a full-time freelancer or entrepreneur has struggled with these questions and has found answers. If that weren’t the case, studies wouldn’t be demonstrating an upward trend in the size of the freelance/self-employed workforce. If you’re considering a new venture, you’re certainly in good company.

In an effort to get over the biggest challenge—fear of failure—let’s examine some common questions that may be keeping you from starting the business of your dreams. After more than two years running a successful (and growing!) freelance venture, I know what I’m talking about—I’ve had to answer each of these questions for myself along my journey.

1. When should I get started?
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If this question is left unanswered you’ll never get started. It may be the scariest question to contemplate because you can put off your start time indefinitely.

You can combat this fear head on by deciding on a firm, but realistic quit day—that’s the day you leave your 9-5 gig behind and embark on your journey as an entrepreneur. Don’t be tempted to live out a crazy quit day fantasy that feels good for a minute but forces you to start your entrepreneur journey before you’re truly ready (i.e. running into your boss’s office with no pants on screaming “I quit!!” before even considering what kind of business you’re going to be starting). And be sure not to burn bridges you might need later. Finally, wait to quit until you’ve saved up an emergency fund that can cover your first few months of non-negotiable expenses (rent, utilities, food and the like).

With some planning, you’ll feel less panicked about this bold move and more prepared to stick to your quit day.

2. What if my idea sucks?
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Pat Flynn lays out his process for validating business ideas in his book, Will it Fly?. He suggests pre-selling products and services before they’re completely ready, to gauge early interest. He also talks about the importance of developing your products/services with audience feedback in mind.

If you’re selling a product (or a productized service), consider releasing it as a minimum viable product (MVP) before completely building it out to include all the features you’ve been dreaming up. This is another great technique for validating a business idea before committing to it completely—and another book to read: The Lean Startup by Eric Ries).

Another way you can test a concept before fully committing to it? Starting your business as a side hustle. Chris Guillebeau is another entrepreneur turned author who lays out an easy-to-follow process for launching a successful side hustle in the adeptly titled Side Hustle. The side hustle concept is also a great way to test if the specific business you want to get into is something you can be happy with over the long term.

Knowledge is power—a key aspect of getting over my own fear of failure had a lot to do with seeking out the expertise of others who have been in my shoes. Before you get too deep into planning a new business venture, seek out the guidance of mentors who have already been down the road you’re just now exploring. If no one immediately comes to mind, consider joining a networking group like your local chapter of Freelancers Union.

3. What if I suck?
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Ah yes, imposter syndrome is real. You’d be hard-pressed to find an entrepreneur who hasn’t experienced this feeling.

When you’re just getting started, or just about to start, it’s easy to give into these feelings as if they were the absolute truth.

Here’s the thing: you won’t get better unless you throw yourself into your work. It’s a self-fulfilling prophecy for becoming an expert. Stay up to date on what’s going on in your industry and make it your goal to constantly be learning new things. Before you know it, you’ll start to feel less and less like an imposter and more and more like you belong. Ultimately, the only way to stop feeling like an imposter is to push through the feeling and refuse to allow it to cripple your progress.

4. What if I bite off more than I can chew?
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If you have a hard time handling stress, then the entrepreneur life is probably not for you. As a business owner you shouldn’t expect to avoid stress, rather you should be focusing on learning strategies for managing it.

Find methods of organizing your business in a way that helps you feel better about what you’re doing day to day. Also, make sure that you regularly celebrate your wins instead of dwelling too deeply on problems. And be sure to maintain your personal life! Get away from the computer, move your body and spend time with your family and friends. Consider it an essential part of running a successful business.

5. [Name of Friend] failed doing the same thing: how can I possibly succeed?
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First off, your experience will be different than anyone else’s. Know this and embrace it. You are not your friend and your friend is not you.

Second, try to think about this question from a different perspective—a positive perspective. For example, if people can find success running their own businesses—and millions are, just give it a Google—why can’t you? As negative thoughts pop into your mind, work to actively and logically manage them.

6. [Name of Client] just dropped me. How will I bounce back?
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Failure can be defined in terms of many different things. There are big failures and small failures. Know that one bad or lost client won’t make or break your business. Yes, even if they’re a big client who pays most of your bills. There are plenty of others to go around, just waiting to hear about what you have to offer. Besides, severing ties with a client who isn’t working out means that you’ll have more time and energy to find someone better to replace them.

One negative client, day, or month won’t define your business. Commit to giving your venture your full efforts over the long run and it will be easier to handle short-term challenges and stressors.

7. How will this turn out?
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Before becoming an entrepreneur, accept that you won’t truly know the answer to this question until you give your business an honest try.

But you don’t have to do it alone. Seek guidance from a mentor and other experts within your industry. Even if you don’t have a go-to person, follow industry influencers who document their processes, wins and failures. They will be the case studies for your efforts.

While you’re in the planning stages of starting a new business, you’ll also want to start developing a “squad” of professionals and advisors that can guide you through all of the specific aspects of setting up your business. At minimum, find a lawyer and accountant you can trust. If finances are tight, seek out your local small business advisory for free guidance.

The more you plan (and learn) on the front-end, the more likely you will be successful. While you can’t completely control what ends up happening, you can certainly stack the deck in your favor with the right foresight and support.

8. What happens if I really do fail?
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Failure looks a lot of ways. You may have heard of (alleged) multi-level marketing scheme, Lularoe. Their independent contractors/sellers brought forth a lawsuit against the company that claims they were pushed into buying thousands of dollars of inventory that they ended up being unable to sell. For these individuals, the consequence of failure was several thousand dollars in credit card debt.

If you fail, you may face similar financial consequences. Or you may not. You may break even and dust yourself off with nothing more than bruised pride. The beauty of starting a business in today’s economy is that you can often do so without expensive overhead like office rent or inventory. Most people start their businesses right from their kitchen table, which means if you fail you’ll still be at your kitchen table.

With regards to Lularoe, a more responsible use of credit cards may have helped these freelancers avoid racking up so much debt. Use their struggle as a lesson— open your own business credit card account, but use it only for things you can realistically pay back.

Every business is different and you’ll have to adapt accordingly. Just don’t forget common sense when it comes to managing your now vulnerable finances. When you’re just starting out, work to secure as many free/cheap tools as possible—if your kitchen table is too small to host meetings, can you use a friend’s living room? If you can borrow business books from the library, do so. Make a list of all the ways you can save money. Every dollar counts when starting your own business.

But through it all, try to avoid thinking so hard about the ways you may crash and burn that you actually set yourself up to fail. Managing your finances is wise, but taking the time to come up with a career backup plan can actually be counterproductive to your business’s success. If you think negatively, those thoughts will become your reality. Take steps to think positively and practice self-care. Don’t throw yourself into work at the expense of spending time with family and doing things that make you happy.

And at the end of the day, it’s OK if you fail. You’ll come back from it. It’s not the end of the world and you will have a learned invaluable lessons along the way. When it comes down to it, it’s better to try and fail than to never try and live with regret.

Just start!
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The most important way to move past fear is to simply get started. There are low risk ways of testing an idea, so why not give your dreams a try?

So jump in! Build your parachute on the way down. There’s nothing more motivating than having bills to pay—you’ll hustle hard until you secure enough income to stay afloat.

Go get it!

What have you done to get over your own fear of failure? Let us know in the comments below.

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This article was written by Maddy Osman. Maddy is an SEO Content Strategist who puts humans at the center of every piece. When she’s not writing, she’s helping Freelancers Union Denver, BMA Colorado and WordCamp Denver run smoothly!